2-Aminopyrimidine-5-boronic Acid Pinacol Ester Chemical Properties

Melting point:

209-211°C

Boiling point:

394.8±34.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)

pka

3.66±0.10(Predicted)

form 

solid

color 

white to off-white

Water Solubility 

Slightly soluble in water. Soluble in chloroform.

InChI

InChI=1S/C10H16BN3O2/c1-9(2)10(3,4)16-11(15-9)7-5-13-8(12)14-6-7/h5-6H,1-4H3,(H2,12,13,14)

InChIKey

BPQVMIDUTRJYSC-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(B2OC(C)(C)C(C)(C)O2)C=N1

Safety Information

Hazard Codes 

Xi,Xn,T

Risk Statements 

36/37/38-22-25

Safety Statements 

26-36/37/39-36/39-45

RIDADR 

UN 2811 6.1 / PGIII

TSCA 

No

HazardClass 

IRRITANT

HS Code 

2933599590

2-Aminopyrimidine-5-boronic Acid Pinacol Ester Usage And Synthesis

Chemical Properties

Light Beige Solid

Uses

2-Aminopyrimidine-5-boronic Acid Pinacol Ester is used in the preparation of phosphoinositide-3-kinases (PI3K) inhibitors.

Synthesis

General procedure for the synthesis of 2-aminopyrimidine-5-boronic acid pinacol ester from 2-amino-5-bromopyrimidine and bis(pinacolato)diboron and 5.9 g (60.3 mmol) potassium acetate: 3.5 g (20.1 mmol) 5-bromopyrimidin-2-amine, 5.6 g (22.1 mmol) bis(pinacolato)diboron, and 5.9 g (60.3 mmol) potassium acetate were dissolved in 35 mL of 1,4-dioxane and subsequently 1.41 g (2.01 mmol) of bis(triphenylphosphine)dichloropalladium(II) was added. The reaction mixture was stirred at 110 °C for 4 hours. After completion of the reaction, it was cooled to room temperature, diluted with ethyl acetate and sonicated for 5 minutes. It was filtered through a diatomaceous earth filled filter and washed with ethyl acetate. The filtrate was washed sequentially with distilled water and saturated saline. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in 100 mL of a solvent mixture of dichloromethane and hexane (1:3, v/v) and stirred at room temperature for 1 hour. It was filtered under reduced pressure and the resulting solid was dried under reduced pressure to give 4 g (yield: 90%) of the target product 2-aminopyrimidine-5-boronic acid pinacol ester.

References

[1] Patent: KR2016/38598, 2016, A. Location in patent: Paragraph 0111; 0112
[2] Organic Process Research and Development, 2016, vol. 20, # 1, p. 95 - 99
[3] Organic Process Research and Development, 2017, vol. 21, # 9, p. 1427 - 1434
[4] Patent: CN106632443, 2017, A. Location in patent: Paragraph 0010-0016
[5] Patent: WO2007/84786, 2007, A1. Location in patent: Page/Page column 89-90

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